Remarkable Activity of a Novel Cyclic Seleninate Ester as a Glutathione Peroxidase Mimetic and Its Facile in Situ Generation from Allyl 3-Hydroxypropyl Selenide

1,2-Oxaselenolane Se-oxide is a novel cyclic seleninate ester that functions as a remarkably efficient glutathione peroxidase mimetic by catalyzing the reduction of tert-butyl hydroperoxide to tert-butyl alcohol in the presence of benzyl thiol. The seleninate ester can be conveniently generated in s...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-10, Vol.124 (41), p.12104-12105
Main Authors: Back, Thomas G, Moussa, Ziad
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Exact sciences and technology
Glutathione Peroxidase - chemistry
Glutathione Peroxidase - metabolism
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Molecular Mimicry
Organic chemistry
Organoselenium Compounds - chemistry
Organoselenium Compounds - metabolism
Preparations and properties
Selenious Acid - chemistry
tert-Butylhydroperoxide - chemistry
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Summary:1,2-Oxaselenolane Se-oxide is a novel cyclic seleninate ester that functions as a remarkably efficient glutathione peroxidase mimetic by catalyzing the reduction of tert-butyl hydroperoxide to tert-butyl alcohol in the presence of benzyl thiol. The seleninate ester can be conveniently generated in situ by oxidation of allyl 3-hydroxypropyl selenide with tert-butyl hydroperoxide. Its catalytic activity surpasses that of several other known GPx mimetics containing cyclic selenenamide structures, which were also tested for comparison.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja028030k